p-Anisoyl chloride → HCID 178488838, compound

HRID 1193573Notes

Reaction equation

HRID 1193573 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[NH2:13])[NH:9][C:8](=[O:14])[CH:7]2[CH:15]([CH3:17])[CH3:16].[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=O)=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:15]([CH:7]1[C:6]2[C:10](=[CH:11][C:12]3[NH:13][C:24]([C:23]4[CH:27]=[CH:28][C:20]([O:19][CH3:18])=[CH:21][CH:22]=4)=[N:3][C:4]=3[CH:5]=2)[NH:9][C:8]1=[O:14])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 21272654HCID 21272654, compound

Product 1

HCID 178488838HCID 178488838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 g. (13.6 mmol) 5,6-diamino-3-isopropylindolin-2-one dihydrochloride were suspended in 10 ml. methylene chloride, mixed with 2.55 g. (15 mmol) p-methoxybenzoyl chloride and 4.55 g. (45 mmol) triethylamine added dropwise thereto at 25° C. The reaction mixture was stirred for 2 hours, evaporated and worked up with water. The residue was heated under reflux for about 24 hours in 75 ml. ethanol and 75 ml. concentrated hydrochloric acid, evaporated and rendered neutral with 2N ammonia solution. The residue filtered off with suction was recrystallised from ethyl acetate/methanol. There were obtained 2.1 g. (48.2% of theory) of the title compound; m.p. 326°-328° C.

Workup

  1. customat 25° C
  2. customevaporated
  3. temperatureThe residue was heated
  4. temperatureunder reflux for about 24 hours in 75 ml
  5. customconcentrated hydrochloric acid, evaporated
  6. filtrationThe residue filtered off with suction
  7. customwas recrystallised from ethyl acetate/methanol
  8. customThere were obtained 2.1 g

Sources & evidence

ORD record
ord-de38eb4b972840169fdf12a17cd6ad7e
Source dataset
uspto-grants-1989_03
Patent number
US04810801

Reaction notes

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